1,1',3,3',5,5'-Hexamethyl-spiro-[furo[2,3-d]pyrimidine-6(5H),5'-pyrimidine]-2,2',4,4',6'(1H,3H,1'H,3'H,5'H)-penta-one.

In the title mol-ecule, C(15)H(18)N(4)O(6), the fused 2,3-dihydro-furan ring has an envelope conformation and the spiro pyrimidine ring has a half-chair conformation. In the crystal, short inter-molecular O⋯C contacts of 2.835 (4) and 2.868 (4) Å between the carbonyl groups indicate the existence of electrostatic inter-actions, which link the mol-ecules into corrugated sheets parallel to the ab plane.

Related literature

For applications of furo[2,3-d]pyrimidine derivatives, see Cody et al. (1997 ▶). For a related crystal structure, see Malathy Sony et al. (2002 ▶).

Experimental

Crystal data

C15H18N4O6

M = 350.33

Orthorhombic,

a = 8.0122 (9) Å

b = 11.9181 (14) Å

c = 16.4037 (19) Å

V = 1566.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 120 K

0.21 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.980, T max = 0.989

15042 measured reflections

1964 independent reflections

1589 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.089

S = 1.01

1964 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019618/cv2553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019618/cv2553Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H18N4O6	Dx = 1.486 Mg m−3
Mr = 350.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 985 reflections
a = 8.0122 (9) Å	θ = 3–25°
b = 11.9181 (14) Å	µ = 0.12 mm−1
c = 16.4037 (19) Å	T = 120 K
V = 1566.4 (3) Å3	Prism, white
Z = 4	0.21 × 0.14 × 0.12 mm
F(000) = 736

Bruker SMART 1000 CCD area-detector diffractometer	1964 independent reflections
Radiation source: fine-focus sealed tube	1589 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→10
Tmin = 0.980, Tmax = 0.989	k = −15→15
15042 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.01P)2 + 2P] where P = (Fo2 + 2Fc2)/3
1964 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.5464 (3)	0.52840 (19)	0.75372 (15)	0.0307 (6)
O2	0.8328 (3)	0.8456 (2)	0.69785 (15)	0.0358 (6)
O3	0.6235 (3)	0.7991 (2)	0.94992 (14)	0.0352 (6)
O4	0.4987 (3)	0.59548 (19)	0.90811 (15)	0.0262 (5)
O5	−0.0582 (3)	0.6474 (2)	0.83863 (15)	0.0333 (6)
O6	0.0962 (3)	0.3545 (2)	1.00229 (15)	0.0306 (6)
N1	0.6700 (4)	0.6929 (2)	0.71936 (16)	0.0247 (6)
N2	0.6981 (4)	0.8365 (2)	0.81937 (16)	0.0251 (6)
N4	0.0212 (3)	0.5008 (2)	0.92003 (17)	0.0242 (6)
N5	0.3017 (3)	0.4687 (2)	0.95490 (17)	0.0242 (6)
C1	0.5068 (4)	0.6811 (3)	0.84600 (19)	0.0229 (7)
C2	0.5782 (4)	0.6254 (3)	0.7708 (2)	0.0250 (7)
C3	0.7394 (4)	0.7956 (3)	0.7427 (2)	0.0254 (7)
C4	0.6170 (4)	0.7750 (3)	0.8785 (2)	0.0252 (7)
C5	0.3186 (4)	0.7229 (3)	0.8311 (2)	0.0276 (8)
C6	0.2301 (4)	0.6208 (3)	0.8654 (2)	0.0242 (7)
C7	0.3382 (4)	0.5599 (3)	0.9086 (2)	0.0236 (7)
C8	0.1355 (4)	0.4355 (3)	0.9614 (2)	0.0237 (7)
C9	0.0562 (4)	0.5958 (3)	0.8712 (2)	0.0258 (8)
C10	0.7301 (5)	0.6431 (3)	0.6434 (2)	0.0334 (8)
H10A	0.6364	0.6084	0.6143	0.050*
H10B	0.8142	0.5858	0.6557	0.050*
H10C	0.7799	0.7016	0.6092	0.050*
C11	0.7816 (5)	0.9384 (3)	0.8465 (2)	0.0321 (8)
H11A	0.7027	0.9851	0.8771	0.048*
H11B	0.8223	0.9802	0.7990	0.048*
H11C	0.8760	0.9186	0.8817	0.048*
C12	0.2810 (5)	0.7474 (3)	0.7410 (2)	0.0337 (9)
H12A	0.1620	0.7645	0.7346	0.051*
H12B	0.3095	0.6817	0.7079	0.051*
H12C	0.3474	0.8119	0.7229	0.051*
C13	0.2770 (5)	0.8270 (3)	0.8822 (2)	0.0358 (9)
H13A	0.1572	0.8428	0.8784	0.054*
H13B	0.3400	0.8915	0.8615	0.054*
H13C	0.3072	0.8134	0.9392	0.054*
C14	−0.1530 (4)	0.4664 (3)	0.9244 (2)	0.0326 (8)
H14A	−0.1596	0.3889	0.9442	0.049*
H14B	−0.2034	0.4712	0.8701	0.049*
H14C	−0.2133	0.5159	0.9619	0.049*
C15	0.4309 (4)	0.3990 (3)	0.9914 (2)	0.0303 (8)
H15A	0.5206	0.4469	1.0123	0.045*
H15B	0.4760	0.3479	0.9501	0.045*
H15C	0.3830	0.3553	1.0363	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0313 (14)	0.0252 (12)	0.0355 (13)	−0.0023 (11)	0.0011 (12)	−0.0009 (11)
O2	0.0412 (15)	0.0304 (13)	0.0357 (14)	−0.0072 (13)	0.0071 (12)	0.0047 (11)
O3	0.0416 (16)	0.0377 (14)	0.0262 (12)	−0.0048 (13)	0.0006 (12)	−0.0017 (11)
O4	0.0207 (12)	0.0275 (12)	0.0304 (12)	−0.0015 (10)	−0.0002 (10)	0.0055 (11)
O5	0.0240 (12)	0.0359 (14)	0.0399 (14)	0.0027 (12)	−0.0043 (12)	0.0057 (12)
O6	0.0257 (13)	0.0307 (13)	0.0353 (13)	−0.0014 (11)	0.0014 (12)	0.0063 (12)
N1	0.0264 (15)	0.0257 (14)	0.0221 (13)	0.0007 (13)	0.0016 (12)	0.0010 (11)
N2	0.0262 (15)	0.0225 (14)	0.0267 (14)	−0.0013 (12)	0.0014 (13)	0.0002 (12)
N4	0.0215 (14)	0.0243 (14)	0.0269 (14)	0.0011 (12)	0.0009 (12)	−0.0002 (12)
N5	0.0228 (15)	0.0228 (14)	0.0268 (14)	0.0009 (12)	0.0004 (13)	0.0025 (12)
C1	0.0207 (15)	0.0247 (16)	0.0234 (16)	−0.0003 (14)	0.0014 (14)	0.0014 (14)
C2	0.0215 (16)	0.0264 (17)	0.0272 (17)	0.0033 (15)	−0.0023 (15)	0.0004 (15)
C3	0.0258 (18)	0.0242 (16)	0.0262 (16)	−0.0007 (15)	−0.0021 (15)	0.0017 (14)
C4	0.0227 (17)	0.0257 (17)	0.0274 (17)	0.0034 (14)	0.0007 (14)	0.0008 (14)
C5	0.0196 (16)	0.0285 (18)	0.0346 (18)	0.0030 (15)	0.0035 (15)	0.0044 (15)
C6	0.0218 (16)	0.0252 (17)	0.0255 (16)	0.0005 (14)	0.0028 (14)	0.0021 (14)
C7	0.0224 (17)	0.0210 (16)	0.0275 (17)	−0.0015 (15)	0.0016 (15)	−0.0016 (14)
C8	0.0225 (17)	0.0243 (17)	0.0244 (16)	0.0015 (15)	0.0015 (14)	−0.0005 (15)
C9	0.0267 (18)	0.0261 (18)	0.0248 (17)	0.0020 (15)	0.0005 (15)	−0.0016 (15)
C10	0.039 (2)	0.0317 (19)	0.0296 (18)	0.0008 (18)	0.0025 (17)	−0.0012 (16)
C11	0.0331 (19)	0.0269 (18)	0.0363 (19)	−0.0054 (16)	0.0001 (17)	−0.0015 (16)
C12	0.0284 (19)	0.0342 (19)	0.038 (2)	0.0031 (17)	−0.0037 (17)	0.0085 (17)
C13	0.0293 (19)	0.0268 (18)	0.051 (2)	0.0024 (16)	0.0097 (19)	0.0012 (18)
C14	0.0195 (17)	0.038 (2)	0.040 (2)	−0.0035 (17)	0.0002 (16)	0.0034 (17)
C15	0.0242 (17)	0.0302 (19)	0.0364 (19)	0.0043 (16)	−0.0023 (17)	0.0091 (16)

O1—C2	1.216 (4)	C5—C13	1.534 (5)
O2—C3	1.206 (4)	C5—C12	1.537 (5)
O3—C4	1.208 (4)	C6—C7	1.334 (5)
O4—C7	1.354 (4)	C6—C9	1.428 (5)
O4—C1	1.443 (4)	C10—H10A	0.9800
O5—C9	1.226 (4)	C10—H10B	0.9800
O6—C8	1.217 (4)	C10—H10C	0.9800
N1—C2	1.378 (4)	C11—H11A	0.9800
N1—C3	1.399 (4)	C11—H11B	0.9800
N1—C10	1.462 (4)	C11—H11C	0.9800
N2—C4	1.378 (4)	C12—H12A	0.9800
N2—C3	1.389 (4)	C12—H12B	0.9800
N2—C11	1.457 (4)	C12—H12C	0.9800
N4—C8	1.380 (4)	C13—H13A	0.9800
N4—C9	1.416 (4)	C13—H13B	0.9800
N4—C14	1.457 (4)	C13—H13C	0.9800
N5—C7	1.358 (4)	C14—H14A	0.9800
N5—C8	1.393 (4)	C14—H14B	0.9800
N5—C15	1.456 (4)	C14—H14C	0.9800
C1—C2	1.513 (4)	C15—H15A	0.9800
C1—C4	1.522 (5)	C15—H15B	0.9800
C1—C5	1.607 (5)	C15—H15C	0.9800
C5—C6	1.516 (5)
C8···O2i	2.835 (4)	C3···O5ii	2.868 (4)
C7—O4—C1	105.6 (3)	O6—C8—N5	121.0 (3)
C2—N1—C3	123.8 (3)	N4—C8—N5	115.8 (3)
C2—N1—C10	117.4 (3)	O5—C9—N4	120.0 (3)
C3—N1—C10	117.2 (3)	O5—C9—C6	126.6 (3)
C4—N2—C3	124.3 (3)	N4—C9—C6	113.4 (3)
C4—N2—C11	116.4 (3)	N1—C10—H10A	109.5
C3—N2—C11	117.3 (3)	N1—C10—H10B	109.5
C8—N4—C9	126.8 (3)	H10A—C10—H10B	109.5
C8—N4—C14	116.9 (3)	N1—C10—H10C	109.5
C9—N4—C14	116.3 (3)	H10A—C10—H10C	109.5
C7—N5—C8	118.5 (3)	H10B—C10—H10C	109.5
C7—N5—C15	122.2 (3)	N2—C11—H11A	109.5
C8—N5—C15	119.1 (3)	N2—C11—H11B	109.5
O4—C1—C2	106.4 (3)	H11A—C11—H11B	109.5
O4—C1—C4	107.4 (3)	N2—C11—H11C	109.5
C2—C1—C4	112.9 (3)	H11A—C11—H11C	109.5
O4—C1—C5	106.5 (3)	H11B—C11—H11C	109.5
C2—C1—C5	111.5 (3)	C5—C12—H12A	109.5
C4—C1—C5	111.7 (3)	C5—C12—H12B	109.5
O1—C2—N1	121.7 (3)	H12A—C12—H12B	109.5
O1—C2—C1	121.7 (3)	C5—C12—H12C	109.5
N1—C2—C1	116.4 (3)	H12A—C12—H12C	109.5
O2—C3—N2	121.8 (3)	H12B—C12—H12C	109.5
O2—C3—N1	120.8 (3)	C5—C13—H13A	109.5
N2—C3—N1	117.3 (3)	C5—C13—H13B	109.5
O3—C4—N2	122.4 (3)	H13A—C13—H13B	109.5
O3—C4—C1	122.6 (3)	C5—C13—H13C	109.5
N2—C4—C1	114.7 (3)	H13A—C13—H13C	109.5
C6—C5—C13	110.2 (3)	H13B—C13—H13C	109.5
C6—C5—C12	114.7 (3)	N4—C14—H14A	109.5
C13—C5—C12	109.2 (3)	N4—C14—H14B	109.5
C6—C5—C1	97.7 (3)	H14A—C14—H14B	109.5
C13—C5—C1	111.8 (3)	N4—C14—H14C	109.5
C12—C5—C1	112.9 (3)	H14A—C14—H14C	109.5
C7—C6—C9	119.0 (3)	H14B—C14—H14C	109.5
C7—C6—C5	109.3 (3)	N5—C15—H15A	109.5
C9—C6—C5	130.4 (3)	N5—C15—H15B	109.5
C6—C7—O4	116.3 (3)	H15A—C15—H15B	109.5
C6—C7—N5	126.4 (3)	N5—C15—H15C	109.5
O4—C7—N5	117.3 (3)	H15A—C15—H15C	109.5
O6—C8—N4	123.1 (3)	H15B—C15—H15C	109.5
C7—O4—C1—C2	−99.4 (3)	C4—C1—C5—C13	−22.4 (4)
C7—O4—C1—C4	139.5 (3)	O4—C1—C5—C12	−141.8 (3)
C7—O4—C1—C5	19.7 (3)	C2—C1—C5—C12	−26.1 (4)
C3—N1—C2—O1	−166.1 (3)	C4—C1—C5—C12	101.2 (3)
C10—N1—C2—O1	−0.8 (5)	C13—C5—C6—C7	−101.6 (3)
C3—N1—C2—C1	19.0 (5)	C12—C5—C6—C7	134.8 (3)
C10—N1—C2—C1	−175.7 (3)	C1—C5—C6—C7	15.1 (4)
O4—C1—C2—O1	35.2 (4)	C13—C5—C6—C9	64.9 (5)
C4—C1—C2—O1	152.8 (3)	C12—C5—C6—C9	−58.7 (5)
C5—C1—C2—O1	−80.6 (4)	C1—C5—C6—C9	−178.4 (4)
O4—C1—C2—N1	−149.9 (3)	C9—C6—C7—O4	−172.6 (3)
C4—C1—C2—N1	−32.3 (4)	C5—C6—C7—O4	−4.3 (4)
C5—C1—C2—N1	94.4 (3)	C9—C6—C7—N5	4.8 (5)
C4—N2—C3—O2	−168.0 (3)	C5—C6—C7—N5	173.1 (3)
C11—N2—C3—O2	−4.5 (5)	C1—O4—C7—C6	−10.5 (4)
C4—N2—C3—N1	11.2 (5)	C1—O4—C7—N5	171.8 (3)
C11—N2—C3—N1	174.8 (3)	C8—N5—C7—C6	−2.2 (5)
C2—N1—C3—O2	172.2 (3)	C15—N5—C7—C6	171.9 (3)
C10—N1—C3—O2	6.9 (5)	C8—N5—C7—O4	175.2 (3)
C2—N1—C3—N2	−7.0 (5)	C15—N5—C7—O4	−10.7 (5)
C10—N1—C3—N2	−172.3 (3)	C9—N4—C8—O6	−179.9 (3)
C3—N2—C4—O3	158.8 (3)	C14—N4—C8—O6	−2.3 (5)
C11—N2—C4—O3	−4.9 (5)	C9—N4—C8—N5	1.2 (5)
C3—N2—C4—C1	−26.5 (5)	C14—N4—C8—N5	178.7 (3)
C11—N2—C4—C1	169.9 (3)	C7—N5—C8—O6	−179.8 (3)
O4—C1—C4—O3	−32.7 (4)	C15—N5—C8—O6	5.9 (5)
C2—C1—C4—O3	−149.7 (3)	C7—N5—C8—N4	−0.9 (5)
C5—C1—C4—O3	83.7 (4)	C15—N5—C8—N4	−175.1 (3)
O4—C1—C4—N2	152.5 (3)	C8—N4—C9—O5	−179.0 (3)
C2—C1—C4—N2	35.5 (4)	C14—N4—C9—O5	3.5 (5)
C5—C1—C4—N2	−91.1 (3)	C8—N4—C9—C6	1.3 (5)
O4—C1—C5—C6	−20.8 (3)	C14—N4—C9—C6	−176.3 (3)
C2—C1—C5—C6	94.9 (3)	C7—C6—C9—O5	176.2 (3)
C4—C1—C5—C6	−137.8 (3)	C5—C6—C9—O5	10.8 (6)
O4—C1—C5—C13	94.6 (3)	C7—C6—C9—N4	−4.1 (5)
C2—C1—C5—C13	−149.7 (3)	C5—C6—C9—N4	−169.5 (3)

Table 1

Selected interatomic distances (Å)

C8⋯O2i	2.835 (4)
C3⋯O5ii	2.868 (4)

Symmetry codes: (i) ; (ii) .